3-(benzo[d][1,3]dioxol-5-ylamino)-5,5-dimethylcyclohex-2-enone | 300689-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 3-(benzo[d][1,3]dioxol-5-ylamino)-5,5-dimethylcyclohex-2-enone
• 英文别名: 3-[(2H-1,3-benzodioxol-5-yl)amino]-5,5-dimethylcyclohex-2-en-1-one；3-(1,3-benzodioxol-5-ylamino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 300689-52-5
• 化学式: C₁₅H₁₇NO₃
• mdl: MFCD01572863
• 分子量: 259.305
• InChiKey: NLZDSJVFDCVUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(benzo[d][1,3]dioxol-5-ylamino)-5,5-dimethylcyclohex-2-enone 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium phosphate 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以19%的产率得到2,2′-thiobis(3-(benzo[d][1,3]dioxol-5-ylamino)-5,5-dimethylcyclohex-2-enone)
  参考文献：
  名称：

  烯胺酮 的C（sp 2）–H键的硫化：使用元素硫作为硫化试剂合成硫醚的方案†

  摘要：

  在CuBr / K 3 PO 4存在下，进行了烯胺酮的C（sp 2）-H键与元素硫的硫化反应。它提供了以中等至良好收率合成硫醚的有效方法。当使用硒粉代替硫粉时，该方案也适用于合成硒化物。

  DOI：

  10.1039/c5ob02619a
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 3,4-亚甲二氧基苯胺 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 3-(benzo[d][1,3]dioxol-5-ylamino)-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  Cu2O-促进邻卤代苯甲酸酯和烯胺酮的级联反应合成异喹啉酮衍生物

  摘要：

  描述了一种实用的 Cu 催化的邻卤代苯甲酸酯与烯胺酮的级联环化以构建异喹啉酮衍生物。该过程涉及 Cu 催化的分子间 C C 偶联和分子内氮杂环化，其中可以耐受多种烯胺酮。

  DOI：

  10.1016/j.tetlet.2022.154287

文献信息

• Three-component domino [3+2] heterocyclization leading to pyran-3-yl-substituted fused pyrroles
  作者：Shuang-Shuang Wang、Qi-Wei Zhu、Shuai Liu、Yang Yang、Zhi-Tong Wang、Bo Jiang、Shu-Jiang Tu

  DOI：10.1007/s11164-013-1396-5

  日期：2015.5

  Concise and efficient three-component domino [3+2] heterocyclization to pyran-3-yl-substituted fused pyrroles promoted by HOAc have been developed under microwave irradiation. The reactions showed broad scopes of substrates which can employ a wide range of readily available arylglyoxal monohydrate and N-aryl enaminones. The structures of products 4 have been unambiguously determined by NMR and HRMS

  在微波辐射下，已经开发出了由HOAc促进的高效高效的三组分多米诺骨牌[3 + 2]杂环化为吡喃-3-基取代的稠合吡咯。反应表明底物的范围很广，它们可以使用各种容易获得的芳基乙二醛一水合物和N-芳基烯胺酮。产物4的结构已经通过NMR和HRMS分析明确确定。的单晶4A通过X射线衍射分析，进一步证实。
• Synthesis of 1,4-dihydroquinoline derivatives under transition-metal-free conditions and their diverse applications
  作者：Xue-Qiang Chu、You Zi、Hua Meng、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1039/c4ob00475b

  日期：——

  A transition-metal-free process for the synthesis of 1,4-dihydroquinoline derivatives starting from simple enaminones with aldehydes via intermolecular cascade cyclization in a one-pot protocol is developed. This methodology affords a variety of products in moderate to good yields. Particularly, the use of the enaminone fragment in 1,4-dihydroquinoline derivatives 3 as a leaving group for further diverse applications with C-nucleophiles is proved to be feasible.

  以简单的烯氨酮和醛为起点，通过分子间级联环化，以一锅协议合成 1,4-二氢喹啉衍生物的无过渡金属工艺被开发出来。该方法能以中等至较高的产率获得多种产品。特别是，将 1,4-二氢喹啉衍生物 3 中的烯丙酮片段作为离去基团与 C-亲核物一起用于进一步的多种应用被证明是可行的。
• Regioselective synthesis of 6-nitroindole derivatives from enaminones and nitroaromatic compounds <i>via</i> transition metal-free C–C and C–N bond formation
  作者：Danhua Ge、Li-Wen Sun、Zi-Lun Yu、Xin-Long Luo、Pei Xu、Zhi-Liang Shen

  DOI：10.1039/d1ob02443d

  日期：——

  Few methods are known for the synthesis of nitroindole derivatives. A simple and practical Cs2CO3-promoted method for the synthesis of 6-nitroindole derivatives from enaminones and nitroaromatic compounds has been developed. Two new C–C and C–N bonds were formed in a highly regioselective manner under transition metal-free conditions.

  已知很少有合成硝基吲哚衍生物的方法。开发了一种简单实用的Cs 2 CO 3促进的烯胺酮和硝基芳族化合物合成6-硝基吲哚衍生物的方法。在无过渡金属条件下，两个新的 C-C 和 C-N 键以高度区域选择性的方式形成。
• Synthesis of functionalized tetrahydrodibenzo[<i>b</i>,<i>g</i>][1,8]naphthyridin-1(2<i>H</i>)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones
  作者：Wenjun Luo、Xinghua Zheng、Fanglian Zhang、Qiuya Luo、Wen-Ting Deng、Lipeng Long、Daohong Yu、Zhong-Xia Wang、Zhengwang Chen

  DOI：10.1039/d3ob01547e

  日期：——

  An eco-friendly and metal-free method for the synthesis of tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones was established. Quinoline-derived dipolarophiles and cyclic enaminones as starting materials undergo a 1,4-Michael addition/SNAr tandem annulation reaction affording the target products. This approach features transition metal-free conditions, good functional group tolerance and operational

  建立了一种环保、无金属的四氢二苯并[ b , g ][1,8]萘啶-1( 2H )-酮的合成方法。喹啉衍生的亲偶极物和环状烯胺酮作为起始原料进行 1,4-Michael 加成/ SN Ar 串联成环反应，得到目标产物。该方法具有无过渡金属条件、良好的官能团耐受性和操作简单性的特点。
• A new and efficient domino strategy to indole derivatives synthesis and its C3-bisfunctionalization
  作者：Li-Yuan Xue、Bo Jiang、Man-Su Tu、Shu-Jiang Tu

  DOI：10.1016/j.tetlet.2012.09.120

  日期：2012.11

  A series of new poly-functionalized indole derivatives were synthesized via domino reactions of alloxan monohydrate and N-aryl substituted enaminones in HOAc at room temperature. The direct C3-bisfunctionalization of indole ring was achieved in a one-pot operation. The reaction is easy to perform simply by mixing common reactants in acetic acid. The reaction proceeds at fast rates and can be finished within 24 min, which makes workup convenient to give good to excellent chemical yields. (C) 2012 Elsevier Ltd. All rights reserved.